Acetic Acid → 1-(2,3-Dimethoxyphenyl)ethan-1-one

Reaktionsgleichung

C[O:2][C:3]1[C:10](OC)=C[CH:8]=[CH:7][C:4]=1[C:5]#N.C[Mg]Br.C[C:17](O)=[O:18].C[CH2:21][O:22][CH2:23][CH3:24]>>[CH3:10][C:3]([C:4]1[CH:7]=[CH:8][CH:24]=[C:23]([O:22][CH3:21])[C:5]=1[O:18][CH3:17])=[O:2]

Komponenten

Edukt 4

HCID 176Acetic Acid

HCID 3283Diethyl Ether

HCID 218622,3-Dimethoxybenzonitrile

HCID 178418573HCID 178418573, Verbindung

Produkt 1

HCID 124074131-(2,3-Dimethoxyphenyl)ethan-1-oneAusbeute 92,5 %

Versuchsvorschrift

To a stirred solution of 2,3-dimethoxybenzonitrile (25)(5.0 g, 30 mmol) in Et2O (12.5 mL) under N2 atmosphere was added methylmagnesium bromide (37% in Et2O) (12.5 mL, 37 mmol). The mixture was stirred for 16 h, and then 50% AcOH (20 mL) was added. After it was stirred for 30 min, the solution was poured into crushed ice, extracted with CH2Cl2, washed with 10% Na2CO3 and then with water, dried over MgSO4 and concentrated. The crude was purified by column chromatography (SiO2, n-hexane: EtOAc=4:1) to give 26. Liquid; yield: 92.5%; 1H-NMR (CDCl3, 200 MHz): δ 2.56 (s, 3H), 3.82 (s, 3H), 3.85 (s, 3H), 6.99-7.02 (m, 2H), 7.13-7.18 (m, 1H); 13C-NMR (CDCl3, 50 MHz): δ 31.18, 55.98, 61.29, 115.83, 120.80, 123.94, 133.62, 148.63, 153.04, 200.26; Anal. calcd for C10H12O3: C, 66.65; H, 6.71. Found: C, 66.60; H, 6.73.